US3155465A - Boron compounds and compositions containing the same - Google Patents

Boron compounds and compositions containing the same Download PDF

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Publication number
US3155465A
US3155465A US182958A US18295862A US3155465A US 3155465 A US3155465 A US 3155465A US 182958 A US182958 A US 182958A US 18295862 A US18295862 A US 18295862A US 3155465 A US3155465 A US 3155465A
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US
United States
Prior art keywords
water
boron
compounds
compound
alcohol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US182958A
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English (en)
Inventor
Gray Richard J De
William O Fitzgibbons
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Standard Oil Co
Original Assignee
Standard Oil Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL290769D priority Critical patent/NL290769A/xx
Priority to NL130552D priority patent/NL130552C/xx
Priority to NL130554D priority patent/NL130554C/xx
Priority to NL130553D priority patent/NL130553C/xx
Priority to NL127614D priority patent/NL127614C/xx
Application filed by Standard Oil Co filed Critical Standard Oil Co
Priority to US182958A priority patent/US3155465A/en
Priority to GB10863/63A priority patent/GB962085A/en
Priority to DEST20420A priority patent/DE1292663B/de
Priority to SE03300/63A priority patent/SE331688B/xx
Priority to ES286442A priority patent/ES286442A1/es
Priority to DK136763AA priority patent/DK102816C/da
Priority to CH385363A priority patent/CH427847A/fr
Application granted granted Critical
Publication of US3155465A publication Critical patent/US3155465A/en
Priority to MY196573A priority patent/MY6500073A/xx
Priority to SE02241/67A priority patent/SE340199B/xx
Priority to NL6906082A priority patent/NL6906082A/xx
Priority to NL6906083A priority patent/NL6906083A/xx
Priority to NL6906084A priority patent/NL6906084A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/04—Esters of boric acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/30—Organic compounds compounds not mentioned before (complexes)
    • C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
    • C10L1/303—Organic compounds compounds not mentioned before (complexes) derived from metals boron compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/06—Organic compounds derived from inorganic acids or metal salts
    • C10M2227/061—Esters derived from boron
    • C10M2227/062—Cyclic esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
    • C10M2227/08—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions having metal-to-carbon bonds
    • C10M2227/082—Pb compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/25—Internal-combustion engines
    • C10N2040/252—Diesel engines
    • C10N2040/253—Small diesel engines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/10—Form in which the lubricant is applied to the material being lubricated semi-solid; greasy
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
    • F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
    • F02B3/00—Engines characterised by air compression and subsequent fuel addition
    • F02B3/06—Engines characterised by air compression and subsequent fuel addition with compression ignition

Definitions

  • R is a member selected from the group consisting of beta alkylene of 3 to 8 carbon atoms
  • x is an integer from 1 to 2
  • R is selected from the group consisting of hydrogen and alkyls of 1 to 2 carbon atoms
  • Z is an oxygenated group containing no more than 10 carbon atoms, selected from the group consisting of R RII
  • R is selected from the group consisting of hydrogen and alkyls of 1-4 carbon atoms.
  • R represents a member of the group consisting of hydrogen, and monovalent hydrocarbon radicals including alkyl, cycloalkyl, aryl, aralkyl, and alkaryl, and R represents a monovalent hydrocarbon radical including alkyl, cycloalkyl, aryl, aralkyl, and alkaryl groups.
  • R in the prior art compound is methyl, ethyl, or propyl, it is extremely difiicult to isolate the tri-ester compounds because they revert back too readily to the diester by releasing alcohol.
  • boron exhibits a strong tendency to form a fourth bond to complete its octet of valency electrons and that the tetracoordinated boron atom has a stabilizing effect on a molecule. It is hypothesized that the oxygen in the aforementioned substituent may facilitate the tetracoordination of the boron atom, with the formation of a hetero ring type structure, of five or six members.
  • NMR spectra were run on 1:1 (molar) hexylene glycol; the methyl ester of hexylene glycol, as representative of Gamers prior art compounds; the methoxy ethyl ester of hexylene glycol, as representative of the compounds of the present invention; and trimethyl borate, as a standard.
  • a boron pro-be was employed.
  • Hexylene glycol borate and the methyl ester of hexylene glycol borate produced identical patterns, namely the same single sharply defined peak associated With the standard trimethyl borate, as indicative of coplanar (trihedral) boron bonding.
  • the conclusion drawn was that the boron bonding in hexylene glycol borate, and in the methyl ester of hexylene glycol borate was identical to that of the standard trimethyl borate, viz. coplanar.
  • the compounds of the invention are capable of essentially completely sterilizing a hydrocarbon-water systern. Their eliectiveness stems from the fact that in addition to being hydrocarbon soluble, they are capable of undergoing limited extraction from hydrocarbon solution into water. In this manner, when a biocidal compound of this invention is added to. a petroleum stock which is then brought into contact with water, some of the original charge of biocide will migrate from the hydrocarbon phase, through the hydrocarbon-water interface and into the water phase, snuffing out life as it goes. It will be apparent that the biocidal effectiveness of these compounds against microbiological life present in a water phase will depend upon the extent to which the compounds undergo water extraction.
  • biocidal additive consisting of two or more compounds of this invention, at least one of which undergoes extensive water extraction and at least one of which undergoes limited water extraction.
  • the extent of water extraction of a given compound may be varied by employing the compound in conjunction with a material which is a mutual solvent for hydrocarbons and for water. This phenomenon will be described more fully hereinafter.
  • the compounds of this invention may be added to any petroleum stock susceptible to degradation by microbiological attack.
  • Specific petroleum stocks contemplated include gasoline, kerosine, diesel fuel, jet fuel, home heating oil, hydraulic fluids, paint solvents, dry cleaning solvents, greases, waxes and lubricating oils.
  • These stocks may contain any of the conventional additives normally associated with them, such as detergents, anti-icing compounds, an-ti-oxidants, gum inhibitors, rust inhibitors, solvent oils, organo-lead compounds, viscosity index improvers, dyes and deodorizers, stabilizers and the like.
  • concentration of biocide required to effect essentially complete sterilization will vary depending on a number of factors including the nature of the petroleum stock to be treated and the density of microbial population vis-a-vis the extent of kill required. Generally an amount of biccide equivalent to 0.0004 Wt. percent elemental boron (based on the weight of petroleum stock) is the minimum concentration which will provide an essentially complete kill. Under some conditions concentrations up to .01 wt. percent boron may be required. While there is no practical upper limit, it can be said that concentrations in excess of 0.1 wt. percent boron cannot generally be economically justified.
  • the compounds of this invention may be prepared by reacting one or more glycol borates or precursors thereof with one or more oxygen-containing alcohols.
  • an oxygen-containing alcohol is defined as an alcohol containing oxygen in addition to that present as a hydroxyl group selected from the group of alcohols consisting of Bit where R, R" and x are defined the same as above in connection with the first disclosed formula. A number of variations of this reaction are shown below.
  • glycol boraltes Specific oxygen-containing alcohols which may be reacted with glycol boraltes according to this invention include:
  • Furfuryl alcohol Tetrahydro furfuryl alcohol l /lethyl-2-furancarbinol Glycidol Diacetone alcohol 4-pentanol-3-methyl-2-one Z-methoxy-l-ethanol 3-methoxy-l-propanol 2-ethoxy-1-etl1anol 2-butoxy-1-ethanol
  • Specific 1:1, 2:2 and 3:2 (molar) glycol borates which may be reacted with oxygen-containing alcohols according to this invention include:
  • 1,3-propylene glycol borate l,3-butylene glycol boratc 2,2-dimethyl-1,3-propane diol borate 2-methyl-2,4-pentane diol borate hereinafter referred to as hexylene glycol borate
  • 2,2-diethyl propane diol borate 2-ethyl-l,3-hexane diol borate 2,2-diethyl propane diol borate 2-ethyl-l,3-hexane diol borate
  • a non-polar hydrocarbon solvent such as isooctane, benzene, toluene, or a xylene
  • Water produced by these reactions can be either removed by azeotropic or other distillation or by chemical absorption. Suitable chemical absorbents include sodium sulfate, calcium sulfate, calcium chloride and the like. Where water is to be removed azeotropically, and the oxygen-containing alcohol employed boils below the azeotrope temperature, it is recommended that the alcohol be added drop-wise to a solventsolution of glycol borate added to a glass bottle:
  • Reaction III has the advantage of obviating the need for a separate step to prepare the glycol borate.
  • the bottle was tightly stoppered, and maintained under slight agitation at 55 C. overnight.
  • the product was separated from the calcium sulfate by filtration.
  • the bottle was tightly stoppered, shaken, and maintained at room temperature until the reaction mix was free of turbidity (indicating that all of the evolved water of reaction had been absorbed by the sodium sulfate).
  • the product was recovered by decantation.
  • the bottle was tightly stoppered, shaken, and maintained at room temperature until the reaction mix was free of turbidity (indicating that all of the evolved water of reaction had been absorbed by the Drierite).
  • the product was recovered by decantation.
  • the resultant series of bottles were mounted along radii of a large rotatable wheel. Wheel was then rotated 7 at 3 r.p.m. for a period of four days, whereby the contents of the bottles were subjected to a substantially continuous sloshing action during the time indicated.
  • a portion of the aqueous phase of each sample was removed from the bottles and plates were poured (on nutrient agar) using a standard centade dilution procedure. The plates were incubated for 48 hours at 30 C. The plates were then subjected to microbiological count.
  • a particularly suitable mutual solvent has been found to be the same oxygen-containing alcohol from which a particular boron compound is formed.
  • the mutual solvent would be methoxy ethanol.
  • R is selected from the group consisting of beta alkylene of 3 to 8 carbon atoms; at is an integer from 1 to 2; R is selected from the group consisting of hydrogen and alkyls of 1 to 2 carbon atoms; and Z is an oxygenated group containing not more than 10 carbon atoms selected from the group consisting of H 0 H H R 0 C- and RC /C ⁇ RI! RI! RI! RI! where R" is selected from the group consisting of hydrogen and alkyls of 1-4 carbon atoms.
  • R BO(CH2)xCHnOCR where R is selected from the group consisting of beta alkylene of 3 to 8 carbon atoms; x is an integer from 1 to 2; and R" is selectedfrom the group consisting of hydrogen and alkyls of 1-4 carbon atoms.
  • a petroleum hydrocarbon stock containing. a compound having the formula where R is selected from the group consisting of beta alkylene of 3 to 8 carbon atoms; x is an integer from 1 to 2; R is selected from the group consisting of hydrogen and alkyls of 1 to 2 carbon atoms; and Z is an oxygenated group containing not more than 10 carbon atoms, selected from the group consisting of O E O H H H where R is selected from the group consisting of hydrogen and alkyls of 1-4 carbon atoms, said compound being present in an amount to provide from .0004 to .01 wt. percent elemental boron based on the weight of hydrocarbon.
  • a petroleum hydrocarbon stock of the jet fuel boiling range containing a compound having the formula where R is selected from the group consisting of beta alkylene of 3 to 8 carbon atoms; x is an integer from 1 to 2; and R" is selected from the group consisting of hydrogen and alkyls of 1-4 carbon atoms, said compound being present in an amount to provide from .0004 to .01
  • x is 1, and R" is hydrogen.
  • composition of claim 8 which additionally contains Z-methoxy-l-ethanol in an amount up to 25 moles per mole of boron compound.
  • composition of claim 9 which additionally contains Z-methoxy-l-ethanol in an amount up to 25 moles per mole of boron compound.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Lubricants (AREA)
US182958A 1962-03-27 1962-03-27 Boron compounds and compositions containing the same Expired - Lifetime US3155465A (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
NL290769D NL290769A (en, 2012) 1962-03-27
NL130552D NL130552C (en, 2012) 1962-03-27
NL130554D NL130554C (en, 2012) 1962-03-27
NL130553D NL130553C (en, 2012) 1962-03-27
NL127614D NL127614C (en, 2012) 1962-03-27
US182958A US3155465A (en) 1962-03-27 1962-03-27 Boron compounds and compositions containing the same
GB10863/63A GB962085A (en) 1962-03-27 1963-03-19 Glycol borate esters and petroleum hydrocarbon compositions containing the same
DEST20420A DE1292663B (de) 1962-03-27 1963-03-20 Verfahren zur Herstellung von 1, 3, 2-Dioxaborinanen
SE03300/63A SE331688B (en, 2012) 1962-03-27 1963-03-26
ES286442A ES286442A1 (es) 1962-03-27 1963-03-26 Un método de preparar compuestos de boro
DK136763AA DK102816C (da) 1962-03-27 1963-03-26 Mineralolieprodukt med forbedret stabilitet over for mikrobiologisk nedbrydning.
CH385363A CH427847A (fr) 1962-03-27 1963-03-27 Procédé de fabrication de composés biocides et utilisation desdits composés pour la protection de produits pétroliers contre les microorganismes
MY196573A MY6500073A (en) 1962-03-27 1965-12-31 Glycol borate esters and petroleum hydrocarbon compositions containing the same
SE02241/67A SE340199B (en, 2012) 1962-03-27 1967-02-17
NL6906082A NL6906082A (en, 2012) 1962-03-27 1969-04-18
NL6906083A NL6906083A (en, 2012) 1962-03-27 1969-04-18
NL6906084A NL6906084A (en, 2012) 1962-03-27 1969-04-18

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US182958A US3155465A (en) 1962-03-27 1962-03-27 Boron compounds and compositions containing the same

Publications (1)

Publication Number Publication Date
US3155465A true US3155465A (en) 1964-11-03

Family

ID=22670793

Family Applications (1)

Application Number Title Priority Date Filing Date
US182958A Expired - Lifetime US3155465A (en) 1962-03-27 1962-03-27 Boron compounds and compositions containing the same

Country Status (9)

Country Link
US (1) US3155465A (en, 2012)
CH (1) CH427847A (en, 2012)
DE (1) DE1292663B (en, 2012)
DK (1) DK102816C (en, 2012)
ES (1) ES286442A1 (en, 2012)
GB (1) GB962085A (en, 2012)
MY (1) MY6500073A (en, 2012)
NL (8) NL6906083A (en, 2012)
SE (2) SE331688B (en, 2012)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1493437B1 (de) * 1965-10-05 1969-10-02 Aral Ag Kraftstoffe fuer Ottomotoren
DE1545482B1 (de) * 1964-12-16 1969-10-23 Aral Ag Verbesserung der Spuelwirkung in bleihaltigen Kraftstoffen fuer Ottomotoren
US5521165A (en) * 1992-09-18 1996-05-28 International Flavors & Fragrances Inc. Insect repellent compositions and methods for using same
US11046717B2 (en) 2019-05-17 2021-06-29 Vanderbilt Chemicals, Llc Less corrosive organoboron compounds as lubricant additives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2437936C2 (de) * 1974-08-07 1983-02-10 Basf Ag, 6700 Ludwigshafen Cyclische Ortho-Borsäureester und deren Verwendung als Bestandteil von Bremsflüssigkeiten

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2767069A (en) * 1954-09-16 1956-10-16 Standard Oil Co Anhydrides of heterocyclic boron compounds
US2839564A (en) * 1952-02-21 1958-06-17 Shell Dev Cyclic esters of boric acid
US2846449A (en) * 1956-08-15 1958-08-05 Du Pont Production of tetrahydrofuran
US2852533A (en) * 1956-02-09 1958-09-16 Brenner Abner Titanium borohydride complex and preparation thereof
US2948597A (en) * 1958-12-30 1960-08-09 Standard Oil Co Novel boron compounds and gasoline containing the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2961459A (en) * 1956-04-27 1960-11-22 Standard Oil Co Glycol pyroborates
US2975135A (en) * 1957-12-30 1961-03-14 Standard Oil Co Lubricating oil composition containing 2:1alpha-glycol borate compounds
NL255514A (en, 2012) * 1959-09-03

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2839564A (en) * 1952-02-21 1958-06-17 Shell Dev Cyclic esters of boric acid
US2767069A (en) * 1954-09-16 1956-10-16 Standard Oil Co Anhydrides of heterocyclic boron compounds
US2852533A (en) * 1956-02-09 1958-09-16 Brenner Abner Titanium borohydride complex and preparation thereof
US2846449A (en) * 1956-08-15 1958-08-05 Du Pont Production of tetrahydrofuran
US2948597A (en) * 1958-12-30 1960-08-09 Standard Oil Co Novel boron compounds and gasoline containing the same

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1545482B1 (de) * 1964-12-16 1969-10-23 Aral Ag Verbesserung der Spuelwirkung in bleihaltigen Kraftstoffen fuer Ottomotoren
DE1493437B1 (de) * 1965-10-05 1969-10-02 Aral Ag Kraftstoffe fuer Ottomotoren
US5521165A (en) * 1992-09-18 1996-05-28 International Flavors & Fragrances Inc. Insect repellent compositions and methods for using same
US11046717B2 (en) 2019-05-17 2021-06-29 Vanderbilt Chemicals, Llc Less corrosive organoboron compounds as lubricant additives

Also Published As

Publication number Publication date
MY6500073A (en) 1965-12-31
DK102816C (da) 1965-10-11
NL6906084A (en, 2012) 1969-07-25
ES286442A1 (es) 1963-08-16
NL290769A (en, 2012)
NL130553C (en, 2012)
CH427847A (fr) 1967-01-15
SE340199B (en, 2012) 1971-11-08
NL127614C (en, 2012)
NL130552C (en, 2012)
GB962085A (en) 1964-06-24
NL130554C (en, 2012)
NL6906083A (en, 2012) 1969-07-25
SE331688B (en, 2012) 1971-01-11
NL6906082A (en, 2012) 1969-07-25
DE1292663B (de) 1969-04-17

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